Dimethyl-2, 2, 2-trichloro-1-n-butyryl-oxyethylphosphonate



DIMETHYL-2,2,2-TRICHLORO-l-N-BUTYRYL- OXYETHYLPHOSPHON ATE No Drawing.ApplicationDecember 17, 1956 Serial No. 628,511

3 Claims. (Cl. 167- 22) The present invention relates to the insecticidefield and more specifically to a novel compound characterized by highinsecticidal activity coupled with relatively low mammalian toxicity.

The amp-trichloro-u-hydroxyethylphosphonic dimethyl ester and itspreparation is described in the Lorenz Patent No. 2,701,225. Thisproduct which is known in the art as dipterex and also as Bayer L 13/59and can be termed chemicallydimethyl-2,2,2-trichloro-l-hydroxy-ethylphosphonate is a potentinsecticide and can be used in insecticide carriers or diluents asdescribed in the patent. The novel compound ofthe present invention isthe n-butyryl derivative of dipterex and can be termed chemicallydimethyl-2,2,2-trichloro-l-n-butyroloxyethylphosphonate. The replacementof the hydroxyl (OH) group at the 1-position on the ethyl group with an-butyryloxy (031110 0) group has been found to result in an unexpecteddecrease in mammalian toxicity. This is illustrated by the followingtable.

T United States Patent 2,927,881 Patented Mar. 8, 1960 "icebutyryloxyethylphosphonate. Upon removal of the solvent by evaporationthe butyrylated product is obtained as an oil and displays C=Oabsorption but no COH absorption in an infrared spectrogram. I

The l-n-butyryloxy compound of the present invention can be employed inplace of dipterex in insecticidal dusts and solutions or emulsions,etc/in the same concentrations as disclosed in the Lorenz patent. Thel-n-butyryloxy compound can also be used to advantage in the fol- TABLEMedian lethal dose mg./kg.

Compound: rat 1 Dipterex 400 Dimethyl 2,2,2 trichloro 1 n butyryl- Ioxyethylphosphonate 3000 Malathion 1000 than the l-n-butyryloxycompound. The iso-butyryloxy compound was also found to have a mammaliantoxicity of about three times that of the l-n-butyryloxy comlowing typecombination formulations. Y

. Example II General household spray formula:

j Percent Pyrethrins .05 Technical Piperonyl butoxide 0.10 Dimethyl2,2,2 trichloro l-nbutyryloxyethylphosphonate 2. Petroleum distillates97.85

100.00 Example 111 Pressurized spray formula:

I Pyrethrins 0.15 Technical piperonyl butoxide 0.50 Dimethyl 2,2,2trichloro 1 n butyryloxyethylphosphonate 2.0 Alkylated naphtha 46.75Methylene chloride 5.0 Freon l2 (CCI F 45.0 Deodorized kerosene 0.6

t 1 Example IV Aerosol formula:

Pyrethrins .25 Technical piperonyl butoxide 1.0 Dimethyl 2,2,2 trichloro1 n butyryloxyethylphosphonate 2.0 Petroleum distillates 11.75Propellant 1 85.0

' (court pound. Tests have also shown the l-n-butyryloxy com- 7 About0.1 mole of dimethyl-2,2,2-trichloro-1-hydroxyethylphosphonate is firstmixed with about 0.1 mole of n-butyric anhydride and heated on a steambath for Other type formulations with and without petroleum distillatessuch as used with DDT and the like can also be employed.

We claim:

1. The compound, dimethyl 2,2,2 trichlorol -noutyryloxyethylphosphonate.

2. An insecticidal composition containing as an essential activeingredient dimethyl-2,2,2-trichloro-l-nbutyryloxyethylphosphonate and aninsecticide carrier.

3. A composition in accordance with claim 2 where the carrier is apetroleum distillate.

References Cited in the file of this patent UNITED STATES PATENTS2,536,647 Kosolapoff Jan. 2, 1951 2,701,225 Lorenz Feb. 1, 1955 FOREIGNPATENTS 509,034 Canada Jan. 11, 1955 7 OTHER REFERENCES Barthel et al.:J. Am. Chem. Soc., 77, 2427 (1955).

2. AN INSECTICIDAL COMPOSITION CONTAINING AS AN ESSENTIAL ACTIVEINGREDIENT DIMETHYL-2,2,2-TRICHLORO-1-N-BUTYRYLOXYETHYLPHOSPHONATE ANDAN INSECTICIDE CARRIER.